Reactions of sulfides with S‐330, a potential decontaminant of sulfur mustard in formulations

Abstract

Because the vesicant sulfur mustard (HD) remains a major chemical threat from either domestic terrorists or countries in conflict, topical preparations are being evaluated as protectants from HD exposure. The objective of this study was to evaluate the effectiveness of chloroamide S‐330 as a potential reactive component in topical formulations. Therefore, the rate, mechanism and by‐products of the oxidation reactions of sulfides by S‐330 in solvent media or specific formulation vehicles were investigated. Using NMR, LC, LC–MS and GC–MS, the reactions of S‐330 with HD, dibutyl sulfide (DBS) and methyl phenyl sulfide (MPS) were studied in acetonitrile, chloroform and perfluoropolyether (PFPE) oil. The oxidation of the three sulfides with S‐330 was very rapid and completed in <4 min in acetonitrile–water or PFPE oil, but the rates of reaction in chloroform were significantly slower. In a large excess of S‐330, the major products resulted from chlorination of the side chains. At a high HD/S‐330 ratio, the major product was HD sulfoxide. Under both conditions, only a trace of HD sulfone, also a blistering agent, was observed. Reactions with DBS and MPS primarily gave sulfoxides and sulfones, with less side‐chain chlorination. The chloroamide S‐330 appeared to be a rapid and effective decontaminant of HD in either polar media or in a PFPE oil. The two alkyl and aryl sulfides are suitable simulants of HD for the initial screening and evaluation of S‐330 or other similar oxidizing agents.

In-situ degradation of sulphur mustard and its simulants on the surface of impregnated carbon systems

“…6). The NMR data was found to be in agreement with the reported information published elsewhere [19,23]. The NMR data was also matched with the pure compounds (sulphoxide and sulphone).…”

“…Heteropolyanion salt (Na 5 PV 2 Mo 10 O 40 ) was supported on microporous carbons and tested against chloroethyl ethyl sulphide (half sulphur mustard) and tetrahydrothiophene [18]. Polyoxometalates reactions were also studied with tropical skin protectant cream [19]. Polyoxometalates were not only used for degradation of the half sulphur mustard but also used for detecting the presence of toxic chemical based on color change of the cream.…”

Kinetics of adsorption of 2-chloroethylethylsulphide on Al2O3 nanoparticles with and without impregnants

“…Metal oxide particles alone show promising results against CW agents, but their efficiency can further be increased by loading/impregnating them with those reactive compounds, which have already been proven to be active against toxic agents [8][9][10][11], however, the possibility of new compounds for impregnation also exists. The use of polyoxometalates (POMs) for impregnation of nanosize metal oxides can be explored with confidence as these have already been proven to be useful for the degradation of toxicants [9][10][11][12].…”

Respiratory Effects of Amifostine and DRDE-07: Probable Prophylactic Agents of Sulphur Mustard in Rats

“…The present method of reducing the toxic effects of SM are by physical and chemical decontamination 7,16,17 .…”

“…The most commonly used decontaminant is Fuller's earth (a native form of aluminium silicate) that removes SM by adsorption, thereby reducing the toxicity 15 . Few chemical decontaminants for human use have also shown very good efficacy [16][17] .…”